S 1 Supplemental Information for : Oxy - Functionalization of Nucelophilic Re ( I ) Metal Carbon Bonds Catalyzed by Se IV

General Considerations: All air and water sensitive procedures were carried out either in a Vacuum Atmosphere glove box under argon, or using standard Schlenk techniques under argon. Labeled solvents, D2O and CD3CN were purchased from Cambridge Isotopes and used without further purification. CD3CN was dried over CaH2 and distilled for NMR used for compound characterizations. 2,2’-bipyridine (Lancaster Synthesis, Inc. 99+%) was sublimed at 100-120°C and stored under argon prior to use. CO5ReBr and rhenium carbonyl ,Re2(CO)10, were purchased from Strem. THF (Mallinckrodt) was refluxed over Na/benzophenone and distilled under argon before use in synthesis or for column chromatography. Basic alumina (EMD) was dried for 2 days at 100 o C in a vacuum oven, and then kept in the glove box antechamber under vacuum overnight before use. 48% aqueous HBr, GOLD LABEL SeO2 (99.9+%), methaneseleninic acid (CH3Se(O)OH, 95%), CH3MgI (Grignard, 3.0M in diethyl ether), CH3I (95.5% stabilized with Cu) and 4,4 ́-Dimethoxy-2,2 ́-bipyridine were all purchased from Aldrich, degassed and stored under argon. 13 CH3I was purchased from Cambridge Isotopes, degassed, and stored under argon. CH3I was vacuum transferred and stored over molecular sieves. GC/MS analysis was performed on a Shimadzu GC-MS QP5000 (ver. 2) equipped with cross-linked methyl silicone gum capillary column (DB5). The retention times of the products were confirmed by comparison to authentic samples. NMR spectra were obtained on a Varian Mercury-400 MHz and a Bruker 400MHz spectrometer at room temperature. All chemical shifts are reported in units of ppm and referenced to the residual protonated solvent. Standard C,H,N elemental analysis was performed by Desert Analytics Laboratory in Tucson, AZ. Fast atom bombardment (FAB) high resolution mass spectra were collected by the University of California, Riverside Mass Spectrometry facility. DIP-CI high resolution mass spectra were collected by the University of Florida, Gainesville, Florida Mass Spectrometry facility. IR Spectra were recorded on a Perkin-Elmer Spectrum One FTIR Spectrometer.